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EP1399413B1 - Composes aromatiques - Google Patents

Composes aromatiques Download PDF

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Publication number
EP1399413B1
EP1399413B1 EP02730486A EP02730486A EP1399413B1 EP 1399413 B1 EP1399413 B1 EP 1399413B1 EP 02730486 A EP02730486 A EP 02730486A EP 02730486 A EP02730486 A EP 02730486A EP 1399413 B1 EP1399413 B1 EP 1399413B1
Authority
EP
European Patent Office
Prior art keywords
methyl
ethyl
compound
perfume
amide
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP02730486A
Other languages
German (de)
English (en)
Other versions
EP1399413A1 (fr
Inventor
Karl Andrew Dean Swift
Kim Joyce Yarwood
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Givaudan Nederland Services BV
Original Assignee
Quest International BV
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Filing date
Publication date
Application filed by Quest International BV filed Critical Quest International BV
Priority to EP02730486A priority Critical patent/EP1399413B1/fr
Publication of EP1399413A1 publication Critical patent/EP1399413A1/fr
Application granted granted Critical
Publication of EP1399413B1 publication Critical patent/EP1399413B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/50—Perfumes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0061—Essential oils; Perfumes compounds containing a six-membered aromatic ring not condensed with another ring

Definitions

  • This invention concerns novel fragrance compounds, and perfumes and perfumed products comprising the novel compounds.
  • WO 9 630 470 describes fragance compositions containing N-ethyl-N-(3-methylphenyl)-propionamide.
  • US 3 909 462 discloses N-phenyl-N-methyl-2-ethyl-butyric acid amide and its use as Odorant and Flavorant.
  • the present invention concerns novel N, N-disubstituted amides, particularly those amides possessing desirable fragrance properties.
  • the amides of the invention can possess fragrance or odour properties which are generally regarded as interesting, pleasant or attractive, typically having fruity or cassis odour properties.
  • This compound thus has the structure and is 2-ethyl- N -methyl- N -(3-methylphenyl)butanamide.
  • this amide is referred to herein as compound 1.
  • Compound 1 has desirable odour properties, generally described as tropical fruit, cassis.
  • Compound 1 has a wide range of chemical stability and so finds potential use in a wide range of products.
  • Compound 1 also has excellent insect repellency properties, equivalent to those of N - N -diethyl-m-toluamide (DET).
  • DET N - N -diethyl-m-toluamide
  • compound 1 has good cloth and hair substantivity properties, having good substantivity on wet cloth and moderate substantivity on dry cloth.
  • Compound 1 might be considered to have some structural similarities to the following known fragrance molecules:
  • Molecule A is known by the Trade Mark Gardamide and has grapefruit, rhubarb odour properties.
  • Molecule B (described in WO 96/30470 of Quest) is known by the Trade Mark Agarbois and has precious wood odour properties. It should thus be noted that the odour profile of compound 1 (tropical fruit, cassis) is very different from those of molecules A and B, in a way that is not predictable. Further, compound 1 is far superior to molecules A and B in terms of additional benefits such as better substantivity properties (both wet and dry cloth substantivity of compound 1 are better than that of molecules A and B). Moreover, the insect repellent properties of compound 1 are superior to those of molecules A and B.
  • amides in accordance with the present invention, and particularly compound 1 might also be considered to have some structural similarities to the molecule, N-phenyl-N-methyl-2-ethylbutyric acid amide which is described in US 3,909,462 as being useful in perfumery on the basis of its herby note.
  • the molecule is also described as possessing a grapefruit aroma. Both of the odour/aroma descriptors given for this molecule are different to the odour properties of compound 1.
  • This compound thus has the structure: and is N , 2-dimethyl- N -(3-methylphenyl)pentanamide.
  • This amide has fruity, cassis, citrus odour properties.
  • the odour properties of the amides of the invention mean that an amide or mixture of amides in accordance with the invention may be used as such to impart, strengthen or improve the odour of a wide variety of products, or may be used as a component of a perfume (or fragrance composition) to contribute its odour character to the overall odour of such perfume.
  • a perfume is intended to mean a mixture of fragrance materials, if desired mixed with or dissolved in a suitable solvent or mixed with a solid substrate, which is used to impart a desired odour to the skin and/or product for which an agreeable odour is indispensable or desirable.
  • amides in accordance with the invention can show good substantivity to hair and cloth, both wet and dry, and hence have good potential for use in fabric treatment products and hair care products.
  • fragrance materials which can be advantageously combined with one or more amides according to the invention in a perfume are, for example, natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc., but also synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, carbocyclic, and heterocyclic compounds.
  • natural products such as extracts, essential oils, absolutes, resinoids, resins, concretes etc.
  • synthetic materials such as hydrocarbons, alcohols, aldehydes, ketones, ethers, acids, esters, acetals, ketals, nitriles, etc., including saturated and unsaturated compounds, aliphatic, carbocyclic, and heterocyclic compounds.
  • fragrance materials are mentioned, for example, in S. Arctander, Perfume and Flavor Chemicals (Montclair, N.J., 1969 ), in S. Arctander, Perfume and Flavor Materials of Natural Origin (Elizabeth, N.J., 1960 ) and in " Flavor and Fragrance Materials - 1991", Allured Publishing Co. Wheaton, Ill. USA .
  • fragrance materials which can be used in combination with one or more amides according to the invention are: geraniol, geranyl acetate, linalol, linalyl acetate, tetrahydrolinalol, citronellol, citronellyl acetate, dihydromyrcenol, dihydromyrcenyl acetate, tetrahydromyrcenol, terpineol, terpinyl acetate, nopol, nopyl acetate, 2-phenyl-ethanol, 2-phenylethyl acetate, benzyl alcohol, benzyl acetate, benzyl salicylate, styrallyl acetate, benzyl benzoate, amyl salicylate, dimethylbenzyl-carbinol, trichloromethylphenyl-carbinyl acetate, p-tert-butylcyclohexyl acetate, ison
  • Solvents which can be used for perfumes which contain an amide according to the invention are, for example: ethanol, isopropanol, diethyleneglycol monoethyl ether, dipropylene glycol, diethyl phthalate, triethyl citrate, isopropyl myristate, etc.
  • a perfume comprises one or more amides in accordance with the invention in an olfactively effective amount. In perfumes an amount of 0.01% by weight or more of an amide according to the invention will generally have a clearly perceptible olfactive effect.
  • the amount is 0.1 to 80% by weight, more preferably at least 1%.
  • the amount of the amide according to the invention present in products will generally be at least 10 ppm by weight, preferably at least 100 ppm, more preferably at least 1000 ppm. However, levels of up to about 20% by weight may be used in particular cases, depending on the product to be perfumed.
  • the invention provides a perfume comprising one or more amides of the invention in an olfactively effective amount.
  • the invention also covers a perfumed product comprising one or more amides of the invention.
  • Amides in accordance with the invention may be readily synthesised, potentially cheaply, from the corresponding amine by reaction with an appropriate acid chloride or anhydride.
  • Preliminary step A is only used when N -methyl-m-toluamide is not available, and is as described in Org. Synth. Coll. Vol. IV (1963), p420.
  • Step B (via the acid chloride) uses the following materials: N -methyl-m-toluamide 121g, 1.0mol Ethylbutyryl chloride 152m1, 1.1mol Triethylamide 167ml, 1.2mol Dichloromethane 1000ml
  • the acid chloride was added to a stirred solution of the N -methyl-m-toluamide in dichloromethane whilst keeping the temperature below 20°C. Once the addition was complete the reaction was left to warm up to room temperature and then poured into water (500ml). The organic and aqueous layers were thoroughly mixed by shaking and once separated the aqueous layer was discarded. The organic phase was washed with a further 500ml portion of water, and then dried with magnesium sulphate.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Detergent Compositions (AREA)

Abstract

Nouveaux composés représentés par la formule (I) dans laquelle R = méthyle, éthyle ou propyle, R1 = méthyle ou H, R2 = méthyle, éthyle ou propyle, R3 = méthyle ou H, R4 = méthyle ou éthyle, R5 = H ou méthyle et dans laquelle R3 et R5 ne représentent pas H ensemble, à l'exception de N-éthyle-2-méthyle-N-(3-méthylphényl) propanamide. Ces composés possèdent des propriétés aromatiques avantageuses, particulières à des fruits tropicaux, une nuance de cassis et peuvent être mis en application dans des parfums et des produits à base de parfum.

Claims (7)

  1. Composé dont la structure est
    Figure imgb0012
     dans laquelle R représente un groupe méthyle, éthyle ou propyle, R1 représente un groupe méthyle ou un atome H, R2 représente un groupe méthyle, éthyle ou propyle, R3 représente un groupe méthyle ou un atome H, R4 représente un groupe méthyle ou éthyle, R5 représente un atome H ou un groupe méthyle, et où R3 et R5 ne sont pas tous les deux un atome H, à l'exception d'un groupe N-éthyl-2-méthyl-N-(3-méthylphényl)propanamide.
  2. Composé selon la revendication 1, dont la structure est
    Figure imgb0013
  3. Composé selon la revendication 1, dont la structure est
    Figure imgb0014
  4. Parfum comprenant un ou plusieurs composés conformément aux revendications 1, 2 ou 3 en une quantité olfactivement efficace.
  5. Parfum selon la revendication 4, dans lequel le composé est présent en une quantité d'au moins 0,01 % en poids.
  6. Parfum selon la revendication 5, dans lequel le composé est présent en une quantité dans la plage de 0,1 à 80 % en poids.
  7. Produit de parfum comprenant un ou plusieurs des composés selon les revendications 1, 2 ou 3 ou un parfum selon les revendications 4, 5 ou 6.
EP02730486A 2001-06-25 2002-06-10 Composes aromatiques Expired - Lifetime EP1399413B1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP02730486A EP1399413B1 (fr) 2001-06-25 2002-06-10 Composes aromatiques

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP01305505 2001-06-25
EP01305505 2001-06-25
EP02730486A EP1399413B1 (fr) 2001-06-25 2002-06-10 Composes aromatiques
PCT/GB2002/002655 WO2003000648A1 (fr) 2001-06-25 2002-06-10 Composes aromatiques

Publications (2)

Publication Number Publication Date
EP1399413A1 EP1399413A1 (fr) 2004-03-24
EP1399413B1 true EP1399413B1 (fr) 2009-09-16

Family

ID=8182056

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02730486A Expired - Lifetime EP1399413B1 (fr) 2001-06-25 2002-06-10 Composes aromatiques

Country Status (6)

Country Link
US (1) US7169748B2 (fr)
EP (1) EP1399413B1 (fr)
JP (1) JP2004536090A (fr)
DE (1) DE60233727D1 (fr)
ES (1) ES2333204T3 (fr)
WO (1) WO2003000648A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3339279A1 (fr) * 2016-12-20 2018-06-27 International Flavors & Fragrances Inc. Nouveaux composés organoleptiques

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU2003260682A1 (en) * 2002-07-18 2004-02-09 Quest International Services B.V. Improvements in or relating to perfume compositions
US7343592B2 (en) * 2004-06-17 2008-03-11 International Business Machines Corporation Benchmark synthesis using workload statistics

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE788461A (fr) * 1971-09-06 1973-03-06 Givaudan & Cie Sa Nouvelle substance odoriferante et aromatisante
EP0100615B1 (fr) * 1982-07-27 1987-09-23 Sumitomo Chemical Company, Limited Anilides fongicides
EP0819161B1 (fr) * 1995-03-25 2001-07-11 Quest International Substance de parfum
GB9721587D0 (en) 1997-10-10 1997-12-10 Quest Int Perfume composition

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP3339279A1 (fr) * 2016-12-20 2018-06-27 International Flavors & Fragrances Inc. Nouveaux composés organoleptiques

Also Published As

Publication number Publication date
DE60233727D1 (de) 2009-10-29
US20040157765A1 (en) 2004-08-12
WO2003000648A1 (fr) 2003-01-03
JP2004536090A (ja) 2004-12-02
US7169748B2 (en) 2007-01-30
EP1399413A1 (fr) 2004-03-24
ES2333204T3 (es) 2010-02-18

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